| 3-Alkenylation or 3-Alkylation of Indole with Propargylic Alcohols: Construction of 3,4-Dihydrocyclopenta[b]indole and 1,4-Dihydrocyclopenta[b]indole in the Presence of Different Catalysts. | |
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MedLine Citation:
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PMID: 22509725 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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3-Alkenylation or 3-alkylation of indole with propargylic alcohols could be efficiently controlled by the catalyst. In the presence of triflic acid, 3-alkenylation of indole occurred and 3,4-dihydrocyclopenta[b]indole skeleton was effectively constructed in moderate to excellent yields via a cascade process. In the presence of Cu(OTf)2, 3-alkylation of indole resulted in the formation of 3-propargylic indole which could be further converted into 2-iodo-1,4-dihydrocyclopenta[b]indoles in the presence of N-iodosuccinimide and boron trifluoride etherate. Possible mechanisms related to the 3-alkenylation or 3-alkylation of indole and their extension to the formation of 3,4-dihydrocyclopenta[b]indoles or 1,4-dihydrocyclopenta[b]indoles were postulated and discussed. |
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Authors:
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Li Zhang; Yuanxun Zhu; Guangwei Yin; Ping Lu; Yanguang Wang |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-4-18 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: - Publication Date: 2012 Apr |
Date Detail:
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Created Date: 2012-4-18 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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